The Other Side of the Fence
by Avoline Malfoy
Summary: How he wound up in this position, he didn't really wanna explain. But he only knew of two that could help him. Didn't mean he was going to out right tell them how to fix this. He didn't like the solution one bit, but he'd rather it be one of the two brothers to fix this than some random stranger. Basically, a collection of gender-bending one-shots.
1. Gabriel

_Disclaimer: I own nothing_

* * *

 _I have no idea where this came from, but I'm gonna run with it, cause I'm a sick, twisted bitch._

 _Now, a few warnings for those sensitive ones. There is gender bending (like, one character), light BDSM, threesome, heavy teasing, mentions of (but not actual) rape, and who knows what else that I have no clue how to categorize. Also, it might get confusing. So, if you don't like any of those, back away now._

 _Sit back and enjoy!_

 _Love always,_

 _Avoline_

* * *

How he wound up in this position, he didn't really wanna explain. But he only knew of two that could help him. Didn't mean he was going to out right tell them how to fix this. He didn't like the solution one bit, but he'd rather it be one of the two brothers to fix this than some random stranger.

Well, Gabriel wasn't sure that was much better, honestly.

"What the fuck," he heard from behind the door of the bunker. Did they really think the angels didn't know about the bunker? The door opened, and Sam stood before him.

Or, more accurately, her.

"Sam," Gabe greeted. "Long story. Please don't make me explain." The confused look on the hunter's face let the archangel know that he was clueless as to who he was. "It's Gabe. I'm a chick, I know." Sam stepped back and allowed her... him... in.

"I know you said don't explain," he began, following Gabriel down the steps. "But how on Earth did you wind up like this?"

"First off, where's Dean," the angel began.

"Right here," the older brother called from a table. "Hey, beautiful. How did you happen on us?" Gabe rolled his... her... eyes.

"Do I need to repeat the Mystery Spot, but swap the roles," she sneered. Gabe figured if he was going to be stuck as a girl, he could at least use the proper pronouns. She grinned at the shocked look on the eldest Winchester's face.

"Gabriel," he spat.

"The one and only," she sighed. "Look, I haven't found a mirror, so can one of you at least tell me if I'm hot?" Dean chuckled before taking a bite of what had to be a delicious burger.

"You look like a blond Emma Watson," he answered. "Kinda hot, really. Wouldn't you agree, Sammy?" She raised an eyebrow before turning to the giant of a man.

"Before you answer that question, let me explain even though I really don't want to," she rushed. "I got it on a day or two ago with a chick. Cute little thing, looked to be about eighteen. Moaned like a porn star, let me tell you." She groaned and plopped into a chair, anxiety swirling in her gut at the predatory look in the green eyes. "I didn't know she was sixteen! And I sure as fuck didn't know that Mommy Dearest was a witch!"

"So you're cursed like this," Sam questioned, his voice far too smooth for Gabriel's comfort.

"Yes," she answered cautiously. "And any male I come near instantly wants to jump my bones. And, this is the cherry on top, the witch made me a total female virgin."

"How do we fix this, before I lock me and you in my room," Dean growled. She swallowed hard, attempting to disappear into the chair.

"That's what I'm worried about," she muttered. "In order to break the curse, I have to..." She shifted her gaze between the two, pleading with them to not make her finish it. "Come on, don't make me say it. I'm nervous enough about it."

"Then maybe Dean should go first," Sam suggested. "He's gentler. And if that doesn't break the curse..." He placed a hand on either arm of the chair, effectively trapping the helpless being in it. "...you're mine." Gabriel shrank back, terrified at the implications behind those words.

"You know, you could just snap your fingers and not be in that chair," Dean teased. "Or did she curse you to be powerless as well?" Their eyes met, and she saw realization dawn in Dean's gaze. "She did. So, if someone were to attempt to rape you..."

"I couldn't be able to stop them," she whimpered, shifting her stare back to Sam. He backed off, and Gabriel relaxed some. "That's why I came here. I didn't want that to become a possibility." Dean stood, and before she could blink, he was crouched in front of her, a reassuring hand on hers.

"Hey," he soothed. "It's going to be fine, Gabe. We won't hurt you, you know it." His fingers started drawing small circles on her wrist. "Just relax and let me take care of you." She felt the tension bleed away as he leaned forward, his breath gently moving her hair. "I promise, you'll feel amazing." Something, she was sure it was arousal, grew within the anxiety, and she tilted her head to the side. "You know all those things that drive women wild?" She nodded as his lips skimmed her skin, sending small bolts of pleasure through her.

"You're gonna find out why women love them."

His lips connected with the juncture of her neck, his teeth biting the skin, and she gasped at the sensation. The small, minuscule bolts were now tangible, and she tilted her head more to give him more access. Dean growled and sucked harder, and she couldn't stop the moan that passed her lips. Dean bit down, then soothed the bruise with little kitten licks.

"Dean," she breathed, her hand cupping the back of his neck. "Oh, good fuck, don't stop."

"Oh, we're just getting started," he chuckled. "Sammy, you'll have to wait. Gotta get her warmed up first." She heard the younger man chuckled from across the table.

"Go for it," he replied. "We can move to a room once you've got her desperate enough."

Gabriel didn't have time to worry about what Sam had said. She was too focused on the hand that had snuck up her shirt and was currently massaging one of her breast. She arched, pressing the pert mound against his hand. His fingers pinched her nipple, and a sob tore from her throat. If this is what sex felt like for women, he would have to take a female vessel more often.

Her jacket was shoved aside, and the t-shirt was yanked over her head, leaving her exposed to the man causing such wonderful feelings. His breath skimmed across her skin, until he came to the pebbled nipple. She whimpered as his tongue teased it, barely flicking against it, and a warm wetness pooled between her legs. Her fingers gripped his hair, pushing his head closer to her body, and she felt him laugh against her skin.

"A bit eager, isn't she, big bro," Sam called.

"Yeah, just a bit," Dean responded. "You think she's desperate enough?" Gabriel prayed that his answer would be yes, cause she wasn't sure how much more she could take.

"Nah, work her a little longer," was the brunette's reply, and she let out a frustrated groan. A pair of lips closed around her nipple, and she almost screamed at the wave of pleasure.

"Please, I can't," she pleaded, trying to buck her hips against his. He held her down with his free hand, his lips never leaving her breast. "Dean, please."

"All in good time," he mumbled against her skin, lifting her before lying her on the table. "Sammy, I need your belt and for you to hold her arms." She whimpered, and he ran a hand up and down her side. "It's okay, Gabe. Just trust me." He slid his own belt off and secured one of her legs to the leg of the table, then used Sam's belt to secure the other, leaving her spread open. "Tease her if you want, Sammy. Just don't touch her yet." Golden eyes flickered up to the taller man.

"With pleasure," he growled, lowering his lips to her ear. "Which is what we plan to overwhelm you with. Dean is older, sure, but when it comes to this, I'm the one you need to worry about. I run this show." She gasped as the blond's breath floated across her heated center. "Do you know what we have planned for you now that you're stuck like this? I plan on letting Dean tease you, pushing you closer and closer to the brink before backing off and leaving you wanting more. I plan on denying you that wonderful bliss until you can't even form a coherent thought, much less speak." She arched off the table when a pair of lips attached to her clit. But Sam didn't stop his verbal torment.

"I plan on taking you every way I can think of, until you're so overcome with pleasure that you can't move. I plan on fucking you thoroughly, on every surface I can find, only stopping when I damn well please. And Dean? Oh, I plan on letting him do the same, fucking you unconscious, then starting back up when you wake. And we'll make you put that non-stop mouth of yours to good use. Been teasing us with those damn suckers. Starting to think you've been practicing, knowing this would eventually happen."

A wordless moan tore from her throat, Dean's tongue flicking against her little bundle of nerves. Sam's grip on her wrists stopped her from reaching for his brother, but it didn't stop her from struggling to do so. The older man rubbed two fingers against her opening before sliding one of them in, and she felt the tension that had been coiling in her gut grow impossibly tight.

"Oh, no you don't," Sam breathed, reaching for Dean's head and forcing him away from her. She groaned in protest, so close to the sensation she's only ever seen. "Take it easy, Dee. Let's drag this out for a while." Dean nodded and stood.

"My room," he gasped. "And we can put that mouth to use."

The belts disappeared, and she was being lifted and carried. The coil was beginning to loosen, and she growled in frustration. Dean tossed her onto the small bed, and she yelped at the action. Her eyes flew open to see him shed his shirt and unbutton his jeans.

"Not looking for perfect," he soothed as her eyes widened. "But if the witch wants you to feel the way most women do, this is part of it. If you don't like it, we'll back of."

Gabriel was shocked to find that he wanted that. She knelt on the bed, eager to taste the hunter on her tongue. He kicked his jeans away, and she licked her lips at the sight of the long, thick cock attached to him. He stepped closer, taking her hand and guiding it to his member.

"Treat it like it was your own," he instructed, and she began to stroke with a firm grip. "Oh, yeah. Just like that. Get comfy with it. Experiment a bit if you want." A groan came from the door, and she shifted her gaze to see Sam palming himself through his clothes.

A rush of lust came over her, and she wondered if she could tease the darker man while pleasuring Dean. She leaned forward and ran her tongue over Dean's tip, relishing the deep moan that fell from his lips. Growing bold from the sound, she took as much as she could in her mouth without gagging and treated it like her favorite candy. A hand tangled in her hair, gripping tightly, and she worried that he would try and force her to take more.

"Oh, fuck yeah," the two men groaned, and she hummed around the engorged member. It quickly vacated the warmth, and she chased after it.

"I don't plan on cumming in your mouth," the green-eyed man growled. "I'd rather fuck you senseless first." She let out a whine before he pushed her onto her back.

"Stand down, Dean," Sam ordered. "I wanna taste her first." Her arousal spiked even higher at his words, and she didn't care if he tied her down or not, so long as she could feel that wonderful sensation Dean has exposed her to.

"You want the belts or the cuffs," the older brother inquired. "I've got the cuffs in my bedside table." A predatory glint shone in Sam's eyes, and Gabriel swallowed in anticipation.

"Cuffs," he answered, holding his hand out to accept the object. She whimpered as Dean handed the silver cuffs over, and Sam wasted no time securing her hands to the headboard. She squirmed, the roaring fire within her slowly fading. "Gonna make you scream my name, Gabriel. Gonna make you so hoarse you can't drive us crazy anymore." His large hands gripped her hips.

In the blink of an eye, his mouth was assaulting her sex.

She cried out in ecstasy, the fire returning almost full force. His tongue tormented her clit, then slid down to probe at her entrance, before sliding back up and teasing her magic button some more. Her eyes slammed shut, and she arched at the tidal wave of pleasure rushing over her. His teeth grazed her skin, and she couldn't stop the scream that passed her lips. He pulled back and jammed two fingers into her, causing her to scream again.

But he didn't move, instead just letting them sit within her.

"Say my name," he snarled. "Say it like it's the only prayer that'll save your life." Her eyes met his, and she panted at the pure lust in his stare.

"Sam," she breathed, and was rewarded with movement. Unfortunately, it only added to the torment, the motions agonizingly slow and almost cruel.

She wasn't above begging. If that's what they wanted out of her, she would gladly do so.

"Please," she pleaded again. "Sam, Dean, please. I can't take anymore. I need more. I need to cum. Please."

"Good fuck, she begs so prettily," Dean groaned.

"Very much so," his brother agreed, removing his fingers, much to her protest. "Calm down. I'll be back. But, like I said earlier, Dean's gentler. It won't hurt as bad with him." She flickered her gaze to the green-eyed man as he approached. He climbed over her, holding himself on his arms to keep from crushing her below him.

"It's gonna be okay, Gabe," he soothed, kissing her forehead. "Gonna take it easy. Don't want to hurt you too much." He grasped himself and rubbed the tip against her drenched folds. "I'm gonna slide in, okay? It's gonna feel weird, but I promise, I'll make you feel so good." She nodded, not trusting her voice to work properly. He pushed against her gently, the head of his cock slipping in. It did feel weird, but she trusted him.

"Dean, get the hell on with it," Sam snapped.

"Patience, Sammy," Dean answered, pulling back and pushing in another inch. "If I move too fast, it'll ruin everything. She came to us cause she trust us. I'm not gonna turn around and hurt her because you're in a big goddamn hurry." The taller man snorted, but was otherwise silent. "Sorry about the language, Gabe."

"Don't care right now," she gasped as he pushed in another inch, meeting the barrier that proved the cursed virginity. "Oh, fuck, this feels good." He chuckled, confusing her for a moment.

"It won't feel all the great here in a second," he responded before pushing past the thin membrane and seating himself fully withing her.

Dear God, the pain. She couldn't put a word to the sound she made, and she trembled in his embrace. He held himself up with one hand, the other drawing soothing circles on her stomach. Tears formed in her eyes, and she tried her damnedest to keep them from falling.

"Relax, sweetheart, relax," he murmured. "It'll fade, I promise. I won't move until you tell me to. Once it fades, just let me know, and I'll make the pain worth it. I swear."

The more he spoke, the more the pain began to bleed out, replaced with a faint feeling of pleasure. She wondered if this is what it felt like, sex from the other side of the union. She flexed the muscles surrounding his dick, and was rewarded with a helpless moan.

"Move," she instructed softly. "It doesn't hurt anymore. You can move."

He pulled out slowly, then slammed back in, brushing against a spot inside of her that made her scream for the third time. It was almost embarrassing how quickly her orgasm was building, but after the relentless teasing she had received, it wasn't all that surprising. Yet, she held back, hoping to last a little while longer. It seemed, though, that Dean wasn't having it. He picked up speed, slamming into that spot with each thrust of his hips.

"You feel so damn good," he groaned in her ear. "So tight, so perfect. Gonna have to take a female vessel more often." She keened and arched into him. "Sam, you might have to take care of yourself. She's not gonna be conscious once I get done. Too damn tense for her to be worth a damn once she breaks loose."

"I'm fine with that," the younger man answered, and Dean began to fuck her in earnest. She pulled against the cuffs, feeling the cold metal bite into her skin, her whole body drawing taut with pleasure.

"Dean," she forced out. "So close."

"So am I, baby," he replied, the affectionate term slipping from his lips. "Cum for me. Let me see you come undone."

She screamed her release, the coil that had been tightening in her gut breaking. She felt like she was flying, every nerve in her body on fire. His voice roared in her ear, and she felt him swell within her as his own orgasm overtook him. His strong arms wrapped around her as they both came down from that wonderful high.

The last thing she remembered before falling asleep was his fingers combing her hair.


	2. Crowley Part 1

_Disclaimer: I own nothing_

* * *

 _I'm gonna guess that it was a hit. So, I'll write more, flipping through characters and over all enjoying myself._

 _So, how will Crowley handle being turned into a woman? And who would be crazy enough to show him how much fun it can be?_

 _Sit back and find out!_

 _Love always,_

 _Avoline_

* * *

Crowley growled as he stared into the mirror. Rowena had struck again, turning him into a woman. He was rather pretty, he would admit. But it just seemed wrong. His facial hair was gone, he was at least two inches shorter, and his prick, which he had sold his own soul for, was gone. And his damn hair was getting in his eyes. He was too used to having shorter hair than this shoulder length mop.

And, damn it all to hell, he looked just like Rowena.

"Damn," Dean's voice called. "Wasn't aware hot chicks could appear just like that." Crowley turned, sneering at the hunter.

"News flash, Squirrel," he snapped. "I happen to be a man, stuck like this, thanks to my MOTHER!" The taller man paused, then doubled over laughing. "Oh, keep laughing, you twit!"

"Did she happen to add in anything that made every man within a mile wanna jump your bones," the blond inquired. Crowley's eyebrow slid up to her hairline. "Gabriel got struck with a similar spell for banging the daughter of a witch. He raced here to keep from getting drug to an ally." The Scotsman shuddered at the thought, thankful to be in the bunker for once.

"I don't believe so," she answered. "But no amount of trying can turn me back into a man. Even the suit is tailored to this body!" Dean nodded. "I've possessed females before. But I never wanted to be stuck as one."

There was something about the way Dean was looking at her that had her pausing her train of thought. It was as if he thought she was the most beautiful thing he had ever seen, and she wondered if that's how he got women to quite literally jump in his bed. Those smoldering eyes were intoxicating, and she really found him attractive. Maybe being stuck as a woman wouldn't be that bad.

"Want me to find out if she re-virginized you," the blond offered. Crowley froze at the idea. "It won't hurt, and I won't even have to penetrate you unless you want me to." She licked her lips, mulling the idea over in her head.

"Fine," she muttered, reaching for the buttons of the suit jacket. A calloused hand closed around her wrist.

"Allow me," Dean implied smoothly, and Crowley found herself moving her hand to let him undress her.

But she soon found that Dean had other plans.

His lips skimmed her cheek before moving against her jawline. The small wave of pleasure had her closing her eyes, her head shifting to the side to give him more room. The tie was loosened, the top few buttons popped, and the hunter was placing open-mouth kisses along her neck. She tilted her head further, dropping the suit jacket and giving him an insane amount of room. The small waves were now stronger, and she couldn't stop the soft moans from passing her lips. She felt him backing her up, and really couldn't care at that point.

"Enjoying this, Crowley," Dean murmured against her skin, sending small vibrations through her body. She nodded in reply. "I'm just getting started."

She bumped into the small bed and tumbled onto it. Her eyes watched as he climbed on top of her, caging her with his arms and legs. Yet the vulnerability only sent her arousal skyrocketing, and she began to pant slightly as he gently unbuttoned the rest of the shirt. He gestured her to sit up, pushing the cotton down her arms, before unclasping the bra and ditching it as well. Before Crowley could blink, she felt both of her nipples being pinched and twisted, sending powerful bolts of excitement straight to her core. A soft groan slipped passed her lips, turning into a scream as a pair of lips closed around one of the pert buds.

"Dean," she whimpered, only to be answered with a chuckle. Her hips bucked against his thigh as his hands reached for the skirt of the suit.

"Easy there," he breathed against her skin. "The fun's just beginning."

She felt the skirt slide down her legs, followed by the cotton fabric of her panties. She was bare to the blond above her, and yet she was not ashamed. She felt liberated, and more than empowered by the hungry look in his eyes. She wanted him to devour her and show her what she was missing out on. His fingers drew small circles on her skin, the action sending bolts straight to her core and forcing a moan from her throat.

"If you think this feels good, you'll be in for a real treat here soon," he teased smoothly in her ear, his hand moving to her center. She felt wetness pooling between her legs, and she whined so pathetically that she almost felt ashamed of herself. His fingertip grazed her clit, and she screamed at the tidal wave of pleasure. She wanted him to linger there for a while, but the digit went lower, teasing at her entrance.

She arched off the bed as two of his fingers jammed into her.

"Oh, you lucky bitch," he sneered, thrusting shallowly. "She didn't even bother to revirginize you. So we can get straight to the fun." The thrusting became rougher, and she couldn't help but thrash about. A pathetic whine left her mouth when they disappeared. "Sit up and get yourself ready. Time to see if you can give as good as you get." She cracked her eyes open to see him yanking his shirt over his head. His hands flew to his pants, and he shed them with ease, his cock springing free. "Get to it."

She scrambled to her knees and moved toward the edge of the bed. She licked her lips before nervously grasping his member. A soft groan floated through the room, and she leaned forward and licked the velvety head. He swore loudly, giving her the confidence to take his cock in her mouth. His fingers gripped her hair, but she didn't feel any pressure from that grip. Her head moved down his length, then back up, and soon, she had found a rhythm that had him swearing breathlessly.

"So, another one for the gender swap?"

She flung herself back and grabbed the blanket to see Sam standing in the door, a predatory glint in his eye. She began to tremble, wondering which of the two would be the lesser of two evils. She couldn't stand either one of them, and they couldn't stand her, but she was so violently aroused and one step from begging for either one of them to just take her and ease this tension within her.

"Yeah, Crowley this time," Dean answered. "Rowena struck him with a similar spell to the one used on Gabe, but this one didn't make her a virgin again."

"So we don't have to be as gentle with her," Sam leered, stepping forward, causing Crowley to shrink away. "Why didn't you call me earlier? You know how much fun I could have with her. And you've got her all worked up already." He strode closer, trapping her between him and his brother. Her fear only ramped the excitement even higher, and she now trembled with a seemingly insatiable need.

"You just love scaring them before fucking their brains out, huh," Dean pointed out. Sam nodded.

"Now, let's get down to business."


End file.
